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WO2018162769A2 - Utilisation du dmso pour la synthèse d'oléacéine et d'oléocanthal - Google Patents

Utilisation du dmso pour la synthèse d'oléacéine et d'oléocanthal Download PDF

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Publication number
WO2018162769A2
WO2018162769A2 PCT/ES2018/000016 ES2018000016W WO2018162769A2 WO 2018162769 A2 WO2018162769 A2 WO 2018162769A2 ES 2018000016 W ES2018000016 W ES 2018000016W WO 2018162769 A2 WO2018162769 A2 WO 2018162769A2
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compounds
oleacein
preparation
substituted
alkyl
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WO2018162769A3 (fr
Inventor
José María FERNÁNDEZ-BOLAÑOS GUZMÁN
Inés MAYA CASTILLA
Alejandro GONZÁLEZ BENJUMEA
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Universidad de Sevilla
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Universidad de Sevilla
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/222—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin with compounds having aromatic groups, e.g. dipivefrine, ibopamine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/18—Antioxidants, e.g. antiradicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C07C67/327—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by elimination of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/26—Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/02—Oxygen as only ring hetero atoms
    • C12P17/06—Oxygen as only ring hetero atoms containing a six-membered hetero ring, e.g. fluorescein
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12Y—ENZYMES
    • C12Y301/00—Hydrolases acting on ester bonds (3.1)
    • C12Y301/01—Carboxylic ester hydrolases (3.1.1)
    • C12Y301/01003—Triacylglycerol lipase (3.1.1.3)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use

Definitions

  • This invention allows doubling the yield of the Krapcho reaction with which oiacein is obtained from oleuropein, present in the olive leaf.
  • Oiecein a dihydroidal dryiridoid present in the virgin and extra virgin olive oil, has very interesting biological properties such as anti-inflammatory and anti-asthmatic.
  • the Krapcho reaction has been extended for the first time to the conversion of oleuropein and ligstroside monoaldehydric aglycones, present in phenolic extracts of EVOO, into the corresponding oleocantai and oleacein dialdehyde derivatives, thereby achieving a very effective method of enrich the phenolic extracts in the io dry dialidohyde ios, of added value.
  • a new procedure for stabilizing and increasing the bioavailability of oleacein and oleocantai by aciiation and acetalation reactions is also described.
  • This invention fits into Production in the areas of Agriculture, Food, Chemistry and Pharmacy.
  • the Activity Sector in which the invention can be used corresponds to the Food and Pharmaceutical Industry area
  • the major components of the phenolic fraction of extra virgin olive oils are the oleacein and oleocantai dialdehydcs, the olealpein and iigstroside monoaldehydric aglycones, and the corresponding felicitc dialdehy aglicons (1).
  • oleocantai has beneficial properties such as anti-inflammatory activity (2; 3) and antitumorai (4; 5).
  • oleocantai exerts a neuroprotective role in the brain (6; 7), being effective in decreasing ⁇ -amyloid plaques which contributes to the prevention of A! Zheimer's disease
  • oleacein is a potent antioxidant and a good inhibitor of the enzyme 5-ipoxygenase involved in the biosynthesis of leukotrienes, so oleacein can be useful in the treatment of asthma and allergic rhinitis (9). It has proven to be an effective drug against diseases related to 7
  • the oieocantal can be isolated from! EVOO (3) or can be prepared from D ⁇ lixosa (14). Oleacein can also be synthesized from D-iixosa (15).
  • Figure 3 Reaction of demeioxycarbonylation of Krapcho on the monoaldehyde aglicons of ia oleuropein 6 and igstrósido 7 followed by acllation.
  • the conversion of oleuropein and igucoside monoaidehyde agiicons into oieacein and oleccantal, respectively, is achieved by heating in wet DMSO.
  • the transformation can be carried out with the monoaidehydic agiicons separately, or with phenolic mixtures ; such as mixtures of isolated olive oil phenoies.
  • This procedure makes it possible to enrich the mixture of phenols in the oieacein and oleocantai dialdehyde secaindoids. facilitating chromatographic isolation of both to reduce the number of components of the mixture.
  • Both diacyated oieacein 2 and oieocantal 9 can be deacylated using lipase or basic catalyst in alcohol in alcohol (RO.
  • the diacyiated dialdehyde derivatives have also been stabilized by transforming them into monoacetic-monoaldehydric derivatives by means of regiosective acetalaclone with etiiengiicol over the unconjugated formyl group, keeping the acid groups on phenolic hydroxides. In this way, more stable derivatives and iipófi ⁇ os can be obtained, and therefore more biodisponib ⁇ es. Subsequent neglect leads to io 3-etiidene acetals of oieacein and oleocantai.
  • the process of converting different secaindoid compounds into oleocantai and oieacein by a variant of demethoxycarbonylation of Krapcho in wet DMSO at alpha temperature in the absence of halide (inorganic salt) is described.
  • This reaction can be carried out on isolated oleuropein, on extracts rich in o! Europeina, on phenolic fractions extracted from extra virgin and virgin olive oil, and on monoaidehydic agiicons of oleuropein and ligstroside isolated.
  • This invention makes it possible to enrich phenolic extracts from olive oil in oieacein and oleocantai at the expense of their monoaidehyde precursors, and facilitate the chromatographic separation of said dialdehyde derivatives.
  • This reaction of Krapcho on the ligstroside leads to oleocantal 8.
  • the acylation of the mixture of 8 and 4 followed by chromatographic separation allows pure oleocantal 9 and diacetyl oleacein 2 to be obtained.
  • the deaciation of 9 to regenerate 8 is carried out for example with Iipase or alcohol base (eOH. Among other aiiphatic alcohols).
  • Oleaee ⁇ na ⁇ 4 ⁇ 2 R-Me (12 mg, 0.038 mmoi) is dissolved in MeOH (1 ml) and ipase from Novozyme 435 Antarctic Candida (12 mg) is added. The mixture is heated at 40 "C for 3 h. Once the reaction is finished, it is microfiltered and concentrated to dryness to obtain the product as an orange syrup. Yield: quant. RF 0.1 ⁇ AcOEt-cyclohexane 1: 1).

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
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  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Biochemistry (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Genetics & Genomics (AREA)
  • Dermatology (AREA)
  • Biomedical Technology (AREA)
  • General Engineering & Computer Science (AREA)
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  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
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  • Psychiatry (AREA)
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  • Oncology (AREA)
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  • Heart & Thoracic Surgery (AREA)
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Abstract

L'invention permet de doubler le rendement de la réaction de Krapcho avec laquelle on obtient l'olacéine à partir d'oleuropéïne, présente dans la feuille d'olivier. L'oléocéine, un sécoiridoïde dialdéhydique présent dans l'huile d'olive vierge et extra vierge, possède des propriétés biologiques très intéressantes en tant qu'anti-inflammatoire et anti-asthmatique. La réaction de Krapcho a pour la première fois été étendue à la conversion des aglycones monoaldéhydiques de l'oleuropéïne et du ligstroside, présents dans des extraits phénoliques de l'AOVE, dans les dérivés dyaldéhydiques d'oléocanthal et d'oléacéine correspondants, un procédé très efficace d'enrichissement des extraits phénoliques en sécoiridoïdes dialdéhydiques à haute valeur ajoutée, étant ainsi obtenu. L'invention concerne également un nouveau procédé pour stabiliser et augmenter la biodisponibilité de l'oléacéïne et de l'oléocanthal par des réactions d'acylation et d'acétalation. L'invention a trait à la production dans les domaines de l'agriculture, de l'alimentation, de la chimie et de la pharmacie. Le secteur d'activité dans lequel l'invention peut être utilisé correspond au domaine de l'alimentation et de l'industrie pharmaceutique.
PCT/ES2018/000016 2017-03-10 2018-03-09 Utilisation du dmso pour la synthèse d'oléacéine et d'oléocanthal Ceased WO2018162769A2 (fr)

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ESP201700241 2017-03-10
ES201700241A ES2690412B1 (es) 2017-03-10 2017-03-10 Procedimiento para la obtención de secoiridoides dialdehídicos

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020136221A1 (fr) * 2018-12-28 2020-07-02 Consejo Superior De Investigaciones Científicas (Csic) Utilisation de sécoiridoïdes pour le traitement de la névrite optique
EP3838885A1 (fr) * 2019-12-16 2021-06-23 National and Kapodistrian University of Athens Procédé de production d'oléocanthal, d'oléacéine et leurs analogues

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3147802B1 (fr) * 2023-04-11 2025-11-28 Univ Montpellier Margines d’huile d’olive

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WO2006122128A2 (fr) 2005-05-09 2006-11-16 The Trustees Of The University Of Pennsylvania Utilisation d'oleocanthal principal d'irrigation dans l'huile d'olive et composants structuralement et fonctionnellement semblables
US20130115202A1 (en) 2005-08-31 2013-05-09 Theta Biomedical Consulting & Development Co., Inc Anti-inflammatory compositions for treating neuro-inflammation
US20160008311A1 (en) 2012-07-14 2016-01-14 Warszawski Uniwersytet Medyczny Oleacein For Treating Or Preventing Diseases Resulting From Atherosclerotic Plaques

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AU2007205147A1 (en) * 2006-01-05 2007-07-19 Deviris Inc. Compounds and derivatives for the treatment of medical conditions by modulating hormone-sensitive lipase activity

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WO2006122128A2 (fr) 2005-05-09 2006-11-16 The Trustees Of The University Of Pennsylvania Utilisation d'oleocanthal principal d'irrigation dans l'huile d'olive et composants structuralement et fonctionnellement semblables
US20130115202A1 (en) 2005-08-31 2013-05-09 Theta Biomedical Consulting & Development Co., Inc Anti-inflammatory compositions for treating neuro-inflammation
US20160008311A1 (en) 2012-07-14 2016-01-14 Warszawski Uniwersytet Medyczny Oleacein For Treating Or Preventing Diseases Resulting From Atherosclerotic Plaques

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Title
ABUZNAIT ET AL.: "Olive oil-derived oleocanthal enhances 0-amyloid clearance as a potential neuroprotective mechanism against Alzheimer's disease: In vitro and in vivo studies", ACS CHEM NEUROSCI, vol. 4, 2013, pages 973, XP055410468, doi:10.1021/cn400024q
CORONA ET AL.: "Inhibition of p38/CREB phosphorylation and COX-2 expression by olive oil polyphenols underlies their anti-proliferative effects", BIOCHEM BIOPHYS RES COMMUN, vol. 362, 2007, pages 606, XP022241411, doi:10.1016/j.bbrc.2007.08.049
DIAMANTAKOS P ET AL.: "Oleokoronal and oleomissional: new major phenolic ingredients of extra virgin olive oil", OLIVAE, vol. 122, 2015, pages 23
FOGLI S ET AL.: "Cytotoxic activity of oleocanthal isolated from virgin olive oil on human melanoma cells", NUTR CANCER, vol. 68, 2016, pages 873
HENEKA ET AL.: "Neuroinflammation in Alzheimer's disease", LANCET NEUROL, vol. 14, 2015, pages 388
HODGE AM ET AL.: "Foods, nutrients and prostate cancer", CANCER CAUSE CONTROL, vol. 15, 2004, pages 11
KARKOULA ET AL.: "Direct measurement of oleocanthal and oleacein levels in olive oil by quantitative H NMR. Establishment of a new index for the characterization of extra virgin olive oils", J AGRIC FOOD CHEM, vol. 60, 2012, pages 11696
LEGENDRE O ET AL.: "(-)-Oleocanthal rapidly and selectively induces cancer cell death via lysosomal membrane permeabilization", MOL CELL ONCOL, vol. 2, 2015, pages e1006077 - 1,8
PARKINSON LKEAST R: "Oleocanthal, a phenolic derived from virgin olive oil: a review of the beneficial effects on inflammatory disease", INT J MOL SCI, vol. 15, 2014, pages 12323
See also references of EP3594198A4
SMITH III AB ET AL.: "Syntheses of (-)-oleocanthal, a natural NSAID found in extra virgin olive oil, the (-)-deacetoxy-oleuropein aglycone, and related analogues", J ORG CHEM, vol. 72, 2007, pages 6891, XP055548540, doi:10.1021/jo071146k
SMITH, III ET AL., J ORG CHEM, vol. 72, 2007, pages 6891
VOUGOGIANNOPOULOU ET AL.: "One-step semisynthesis of oleacein and the determination as a 5-lipoxygenase inhibitor", J NAT PROD, vol. 77, 2014, pages 441, XP055368058, doi:10.1021/np401010x

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020136221A1 (fr) * 2018-12-28 2020-07-02 Consejo Superior De Investigaciones Científicas (Csic) Utilisation de sécoiridoïdes pour le traitement de la névrite optique
EP3838885A1 (fr) * 2019-12-16 2021-06-23 National and Kapodistrian University of Athens Procédé de production d'oléocanthal, d'oléacéine et leurs analogues
WO2021121925A1 (fr) * 2019-12-16 2021-06-24 National And Kapodistrian University Of Athens Procédé de production d'oléocanthal, d'oléaceine et de leurs analogues

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ES2690412B1 (es) 2019-11-13
EP3594198A4 (fr) 2021-09-08
WO2018162769A3 (fr) 2018-11-08
ES2690412A2 (es) 2018-11-20
ES2690412R1 (es) 2019-02-08
EP3594198A2 (fr) 2020-01-15

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